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Showing Compound Limonin (17-beta-D-glucoside-) (FDB097307)

Record Information
Version1.0
Creation date2020-04-02 17:47:17 UTC
Update date2020-04-02 17:47:18 UTC
Primary IDFDB097307
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLimonin (17-beta-D-glucoside-)
Descriptionlimonin 17-beta-D-glucoside, also known as beta-D-glucosyl-limonin, belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. Based on a literature review very few articles have been published on limonin 17-beta-D-glucoside.
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility1.01 g/LALOGPS
logP1.07ALOGPS
logP0.022ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.97ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area214.95 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity150.62 m³·mol⁻¹ChemAxon
Polarizability64.26 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC56H100O6
IUPAC name(1'R,2R,2'R,3S,5'S,7'R,10'R,13'S)-5'-[(R)-(furan-3-yl)({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5',7',11',11'-tetramethyl-8',15'-dioxo-12',16'-dioxaspiro[oxirane-2,6'-tetracyclo[8.7.0.0^{1,13}.0^{2,7}]heptadecane]-3-carboxylic acid
InChI IdentifierInChI=1S/C56H100O6/c1-4-7-10-13-16-19-22-24-26-27-28-30-31-34-37-40-43-46-49-55(58)61-52-53(51-60-54(57)48-45-42-39-36-33-21-18-15-12-9-6-3)62-56(59)50-47-44-41-38-35-32-29-25-23-20-17-14-11-8-5-2/h8,11,15,17-18,20,25,29,53H,4-7,9-10,12-14,16,19,21-24,26-28,30-52H2,1-3H3/b11-8-,18-15-,20-17-,29-25-/t53-/m0/s1
InChI KeyYCBCZIKALKDHRL-ZLSCYYNLSA-N
Isomeric SMILES[H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCCC)(COC(=O)CCCCCCC\C=C/CCCC)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC
Average Molecular Weight869.41
Monoisotopic Molecular Weight868.75199094
Classification
Description Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentLimonoids
Alternative Parents
Substituents
  • Limonoid skeleton
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Delta valerolactone
  • Delta_valerolactone
  • Dicarboxylic acid or derivatives
  • Oxirane carboxylic acid or derivatives
  • Oxirane carboxylic acid
  • Oxane
  • Monosaccharide
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Furan
  • Secondary alcohol
  • Ketone
  • Carboxylic acid ester
  • Lactone
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Oxirane
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Primary alcohol
  • Carbonyl group
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fl9-0000917000-bfe75e7ec80677af9c2d2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0072-0100901000-91640fcc9e33f0e300272017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-009b-4850900000-b638dad6264ab4e29f092017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052k-1100529000-a754f9af4a793a9b833e2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-3100903000-fd0ece833f148ccf75342017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-3001900000-87e3674aa349854cc7f32017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uei-0000509000-fd92c4cb1ff246463ac82021-10-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000149000-669b4353d8af311bff2e2021-10-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-3400792000-99a822f7842a869fe7a92021-10-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000009000-5ec0928b514b7a3680622021-10-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-3000079000-2c963251348416217ee72021-10-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000811000-952e1ff9efa4a74f8ff22021-10-22View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference